Most icebreakers fail for the same reason: they ask people to perform. "Tell us a fun fact about yourself" puts everyone on the spot, and half the room spends the next ten minutes rehearsing instead of listening. Good icebreakers ask for something small and specific that anyone can answer without thinking too hard.
Compare "What are your hobbies?" with "What's the last thing you cooked that you were proud of?" The first gets a list. The second gets a story, and stories are what people remember. The same goes for "Where would you like to travel?" against "What's a place you'd happily go back to next week?"
A few habits make any question work better. Go first, so people see how long an answer should be. Let anyone pass without explaining why. Keep the round short, ideally under a minute per person in a big group. And skip questions about money, relationships or health unless everyone in the room already knows each other well.
Coming up with fresh questions every week is the hard part, especially for teachers and team leads who meet the same group again and again. I keep a few generators bookmarked for that. The conversation starter generator and the random question generator give you a new question whenever you need one, and the random topic generator covers speech, debate and conversation topics when you want something meatier, like a two-minute impromptu talk. They're among the word and game generators on RandoCue, free and with no account needed.
One last tip: if a question falls flat, don't push it. Laugh, say "okay, that one was terrible", and draw another. A group that sees you shrug off a bad question relaxes faster than one that sits through a perfect one.
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